There is a continuing interest in the preparation of synthetic fragrance and flavor compounds and their uses in consumer products. Materials that impart violet, green, melon, and cucumber notes, with a low odor threshold, are of particular interest in the fragrance and flavor industry. Compounds that can impart such notes have proven important in many contexts, including air care products (e.g., candles), in personal care products (e.g., lotions and shampoos), in spray perfumes and colognes, in confections, and in beverages.
Several compounds are known in the art for their high impact violet, green, orris, and melon character. For example, certain C9 aldehydes and corresponding nitriles are known for their use in fragrances and flavors to produce such green, melon and violet notes. Specific nitriles have been shown to be more chemically stable than their corresponding aldehydes and thus can have an advantage for use in fragrances and flavors. In certain instances, corresponding nitriles and aldehydes within a given class can have similar flavors and fragrances. However, not all aldehydes and nitriles have been explored for use in the flavor and fragrance industries. Moreover, compared to aldehydes, a relatively small number of nitriles have been accepted for use in the flavor and fragrance industries. The flavor and fragrance properties of many nitriles can be inferior to those of the corresponding aldehydes, as certain nitriles can tend to have more “chemical” and less natural flavors and fragrances.
By way of example, (2E,6Z)-nona-2,6-dienal has been investigated and has been found to have a strong violet leaf, cucumber and watermelon aroma, and is widely used in the flavor and fragrance industry. (2,6)-Nona-2,6-dienenitrile, the corresponding nitrile, was described by BASF in 1984 (DE 102004009440), while its various stereoisomers have been described for their use as flavor and/or fragrance materials (see, e.g., WO 2006/095200; U.S. Pat. No. 8,007,849; WO 2011/128340; DE 2733857).
(2E)-Non-2-enal (EP1262473) has also been explored and has been found to have an extremely strong, very fatty, oily, waxy orris aroma. Its corresponding nitrile, (2E)-Non-2-enenitrile, known as “Iris Nitrile,” has been cited in the patent literature for its use in the fragrance industry (EP 1884555; WO 2003/070871; DE 10212687).
Additionally, (6Z)-non-6-enal is used in flavor and fragrance compositions for its strong, natural honeydew and cantaloupe melon notes. The corresponding nitrile, (6Z)-non-6-enenitrile, which has the chemical structure shown below as formula (I), is a known material (CAS#80639-54-9; see U.S. Pat. No. 5,543,536; U.S. Pat. No. 5,688,986; J. Chem. Soc. Chem. Comm. 1981, 1081; and J. Organomet. Chem. 1985, 115).

(6Z)-Non-6-enenitrile is also known as cis-6-nonenenitrile. However, (6Z)-non-6-enenitrile has never been used as a fragrance or flavor compound, and its olfactory, aroma, and flavor properties have not previously been documented.
While structurally similar compounds can, in some circumstances, have similar flavor and fragrance properties, their behavior can be unpredictable. Moreover, the stability of untested flavor and fragrance compounds (and of organic compounds generally) can be difficult to predict.
Existing aldehydes and nitriles used as fragrance and flavor compounds can lack fresh, natural aromas and flavors. Certain existing aldehydes and nitriles used as fragrance and flavor compounds can be chemically unstable in certain media, which can limit their incorporation into products. For example, certain existing aldehydes and nitriles can be unstable in bleaches, unstable in products with high pH, and/or unstable in products with low pH. Thus, there remains a need for chemically stable fragrance and flavor compounds that can help to create fresh, natural aromas and flavors.